Investigation On The Synthesis Of Quinoline,Quinazoline And Dicyanoanthrene

Nitrogen-containing heterocyclic compounds are one of the important components in natural products and drugs.Therefore,the development of simple,green,and efficient methods for synthesizing nitrogen-containing heterocyclic compounds has always received widespread attention and is one of the main fields of organic synthetic chemistry.In recent years,green chemistry has been concerned by scientists.Some strategies of green chemistry are to avoid by-products,use recyclable catalysts and reagents instead of non renewable energy,and use low toxic raw materials and solvents.However,in the synthesis methods of nitrogen-containing heterocyclic compounds,we found that most previous synthesis methods had problems such as high temperature,the addition of transition metals,and excessive reaction time.Therefore,it is necessary to find greener synthesis methods from aspects such as raw materials and solvents to achieve better results.In the introduction,we introduced the reactions involved in tert-butyl nitrite(TBN)according to its role in organic synthesis.We also introduced the applications of quinoline compounds,4-aminoquinazoline,9,10-dicyanoanthrene compounds,and their traditional synthesis methods in this chapter.Chapter 2 introduces a simple,green,and efficient method for synthesizing quinoline compounds.We use 2-(1-phenylvinyl)aniline and benzoic acid to react in chlorobenzene as solvent,without catalyst and additives.After dehydration,condensation and CO2 removal,cyclization and aromatization generate 2,4-diarylquinoline.In this method,the substrate range is wide,and both raw materials with electron withdrawing or electron donating substituents can obtain the target product with high yield.Moreover,the reaction temperature is relatively low,the conditions are mild,and the reaction can be successfully completed without the catalysis of transition metals and additives.There are no by-products,providing a new method for synthesizing quinoline compounds.Chapter 3 introduces a method for synthesizing 4-aminoquinazoline compounds.We use o-aminobenzonitrile as the raw material,with the participation of tert-butyl nitrite(TBN)and appropriate amount of potassium carbonate,two molecules of o-aminobenzonitrile are coupled,then cyclization,denitrification,aromatization to obtain 4-aminoquinazoline compounds.In the past,there were shortcomings in the synthesis of 4-aminoquinazoline,such as the need for a catalyst or the need for multiple raw materials to be synthesized together.In the proposed solution in this article,cheap and easily available ethanol is used as the solvent,and there is no transition metal catalysis,which is environmentally friendly.Chapter 4 introduces a method for synthesizing 9,10-dicyanoanthrene and its derivatives from o-iodophenylacetonitrile.During the reaction process,the use of small molecules avoids pre functionalization.This method has the characteristics of low temperature,mild reaction conditions,and simple operation,providing an effective synthesis pathway for the synthesis of useful 9,10-dicyanoanthrene compounds.